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A and C macrocyclic oxidation substituted pentacyclic triterpanoids and preparation method and use thereof

An unsubstituted, compound technology, applied in the field of pentacyclic triterpene derivatives and their preparation, can solve problems such as research in the ascendant

Inactive Publication Date: 2008-02-06
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, research on this enzyme and its inhibitors is in the ascendant

Method used

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  • A and C macrocyclic oxidation substituted pentacyclic triterpanoids and preparation method and use thereof
  • A and C macrocyclic oxidation substituted pentacyclic triterpanoids and preparation method and use thereof
  • A and C macrocyclic oxidation substituted pentacyclic triterpanoids and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of compound Ic

[0039] Compound oleanane-28-carboxylate methyl ester-2,12-diene (1.0mmol) and m-chloroperoxybenzoic acid (2.0mmol) were dissolved in 10 ml of dichloromethane, stirred at room temperature overnight, in the reaction 5 drops of concentrated hydrochloric acid were added dropwise to the mixture, and stirred at room temperature for 4 hours. 10 ml of water was added, and the aqueous layer was extracted with 10 ml of dichloromethane. The organic layers were combined, washed with 10 ml of saturated sodium bicarbonate solution, washed with water until neutral, and dried over anhydrous magnesium sulfate. Silica gel column chromatography (eluent: petroleum ether / ethyl acetate: 8 / 1) gave compound Ib as a white solid with a yield of 50.8%. Compound Ib was added to 5 ml of tetrahydrofuran, 5 drops of concentrated sulfuric acid was added, and the mixture was heated to reflux for 1 hour. Most of the solvent was removed, 5 ml of ethyl ace...

Embodiment 2～ Embodiment 6

[0040] According to the method of Example 1, the compounds of Example 2 to Example 6 shown below were prepared:

Embodiment 2

[0041] Example 2: Preparation of 3β-methylsulfonyloxy-12-carbonyl-oleanane-28-carboxylic acid methyl ester (Ia), C 32 h 52 o 6 S, MS: ESI m / e 564 (M + ); Rf (petroleum ether / ethyl acetate: 3 / 1): 0.54; 1 HNMR (400MHz) δ: 2.61 (brd, 1H, J = 3.6Hz), 2.79 (brd, 1H, J = 13.6Hz), 3.02 (s, 3H, CH 3 S), 3.68(s, 3H, OCH 3 ), 4.33 (dd, 1H, J=4.8, 10.8Hz, H-3).

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Abstract

The present invention relates to a pentacyclic triterpanoid derivative of multiple-oxide substitution of the A ring and the C ring and the medicine salt or solvate of the derivative, and the present invention also relates to the preparation method, the drug combination, and medical use of the derivative. The compound of the present invention has the functions of inhibiting the activity of six human tumor cell strains in vitro, such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cells (CNE), oral squamous carcinoma cell(KB), human lung cancer cell (A549), human hepatoma cell (BEL-7404), and human cervix cancer cell (Hela), and the function of the invention is at the same magnitude of the positive control of cisplatin, thereby the compound can be used as expected antitumor drug. The compound of the present invention also inhibits the alpha glucosidase strongly, and the inhibiting effect is greater than the positive control of acarbose, thereby the compound can be used as expected medicine for preventing and treating diabetes and the treatment of the virus diseases.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular, the invention relates to pentacyclic triterpene derivatives with multiple oxidation substitutions of ring A and ring C, and a preparation method and use thereof. The present invention treats the series of compounds on six kinds of in vitro cultured human tumor cell lines such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cell (CNE), oral epithelial cancer cell (KB), human lung cancer cell (A549), human Liver cancer cells (BEL-7404), human cervical cancer cells (Hela) were screened for tumor cell growth inhibitory activity. The compounds are found to have a certain activity of inhibiting the growth of tumor cells, and can be expected to be used as antitumor drugs. The present invention also finds that such compounds have a strong inhibitory effect on α-glucosidase, and can be expected to be used as medicines for preventing and treating diabet...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07J53/00A61K31/56A61P35/00A61P3/10
Inventor 赵昱陈海永郑汉其巫秀美白骅约阿施·史托克希特
Owner ZHEJIANG HISUN PHARMA CO LTD
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